Dichloromethane → HCID 18931465, compound

HRID 1598968Notes

Reaction equation

HRID 1598968 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH2:4][CH2:3]1.[F:22][C:23]1[CH:33]=[C:32](I)[CH:31]=[CH:30][C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(CC)CC)C.C(Cl)Cl>[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:32]3[CH:31]=[CH:30][C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([F:22])[CH:33]=3)=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 18761561Ethyl 2-fluoro-4-iodobenzoateHCID 18931462HCID 18931462, compound2×

Product 1

HCID 18931465HCID 18931465, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.20 g (0.72 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-N-(4-methylphenyl)-7-ethynylquinoline (Compound 3) and 0.39 g (1.5 mmol) of ethyl 2-fluoro-4-iodobenzoate were added 2.9 g (4.0 mL, 29 mmol) of triethylamine, 0.029 g (0.15 mmol) of copper(I) iodide, and 0.113 g (0.16 mmol) of bis(triphenylphosphine)palladium(II) chloride, consecutively. The resulting mixture was stirred at room temperature for 20 hours. Methylene chloride was added and the reaction was adsorbed onto silica gel. The product was obtained by flash chromatography (5% ethyl acetate in hexanes) followed by recrystallization in ethanol to give the title compound as orange crystals. PNMR (300 MHz, CDCl3) d 1.37 (6 H, s), 1.40 (3 H, t, J=7.1 Hz), 1.86 (2 H, t, J=6.0 Hz), 2.38 (3 H, s), 3.61 (2 H, t, J=6.0 Hz), 4.39 (2 H, q, J=7.1 Hz), 6.77 (1 H, d, J=1.7 Hz), 6.87 (1 H, dd, J=7.9, 1.7 Hz), 7.23-7.28 (7 H, m), 7.86 (1 H, t, J=7.8 Hz).

Workup

  1. customfollowed by recrystallization in ethanol

Sources & evidence

ORD record
ord-f2e3a1033424478480f53a185bcf10f2
Source dataset
uspto-grants-1998_04
Patent number
US05739338

Reaction notes

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